Propyl chloroformate → HCID 25051659, compound

HRID 252589Notes

Reaction equation

HRID 252589 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]([CH2:21][CH3:22])[C:10]3[C:15]([C:16]=2[C:17]#[N:18])=[CH:14][CH:13]=[C:12]([O:19][CH3:20])[CH:11]=3)=[CH:4][C:3]=1[F:23].Cl[C:25]([O:27][CH2:28][CH2:29][CH3:30])=[O:26]>CCOC(C)=O.C([O-])(O)=O.[Na+].O>[CH2:28]([O:27][C:25](=[O:26])[NH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]([CH2:21][CH3:22])[C:10]3[C:15]([C:16]=2[C:17]#[N:18])=[CH:14][CH:13]=[C:12]([O:19][CH3:20])[CH:11]=3)=[CH:4][C:3]=1[F:23])[CH2:29][CH3:30]

Participants

6

Reactant 2

HCID 7998Propyl chloroformateHCID 25051661HCID 25051661, compound

Product 1

HCID 25051659HCID 25051659, compoundYield 63.2%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8857Ethyl AcetateSolventHCID 516892Sodium BicarbonateSolvent

Procedure

A biphasic mixture of 2-(4-amino-3-fluorophenyl)-1-ethyl-6-methoxy-1H-indole-3-carbonitrile (74 mg, 0.24 mmol), prepared as described in example 1Gb, and propyl chloroformate (0.033 mL, 0.29 mmol) in EtOAc (3 mL) and saturated NaHCO3 (3 mL) is prepared at 0° C. and then allowed to warm to room temperature and stirred for 24 h. The reaction is then diluted with H2O and extracted with EtOAc (2×). The organic phases are washed with H2O and saturated NaCl and then dried and concentrated. Flash chromatography (EtOAc/hexanes 10-40%) gives 60 mg (63%) of [4-(3-cyano-1-ethyl-6-methoxy-1H-indol-2-yl)-2-fluorophenyl]-carbamic acid propyl ester as an off-white solid.

Workup

  1. customprepared
  2. customis prepared at 0° C.
  3. extractionextracted with EtOAc (2×)
  4. washThe organic phases are washed with H2O and saturated NaCl
  5. customdried
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-457053abee0b4960b3276a912fe973db
Source dataset
uspto-grants-2011_01
Patent number
US07868037B2

Reaction notes

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